I'm a EMT so we don't get paid that much.
Welcome to the forum and to the hobby.
With respect to some of the gentlemen above, I would not get a basket pipe, a Dr. Grabow, or an unrestored estate. You mentioned $40 as a price. I would check with some of the sponsor sites and look at estate pipes in that price range. Peterson, Savenelli, and Stanwell are all good solid pipes, and if you can find one in your budget you will probably have a winner. I would not advise trying to fix up an estate pipe until you have a little experience.
Tobaccos: You have some experience with cigars, but don't mention what your tastes are. For general advice, let me suggest the following:
Avoid flakes, plugs, etc. while you are starting out. You don't need to deal with preparing tobacco at this stage.
I would call up one of our sponsors that offers a sample pack, like pipesandcigars.com. Talk to them, and get some advice. Pick up an ounce or so of several blends of different types. Don't go out and buy 4 ounces of something somebody recommends. It may be that,if you start with a call to one of these places, and have an amount that you want to spend, they can help you through the whole process. I would bet that for $75 (or less), you can come away with a decent pipe - not a great pipe, but a decent one - a variety of tobacco, and cleaners, pipe tool, etc.
Good luck and have fun.